If you’re a fan of How to Lose a Guy in 10 Days (2003), you know the magic of a perfectly balanced rom-com—witty banter, sizzling chemistry, and a playful battle of the sexes that keeps you hooked. Starring Kate Hudson and Matthew McConaughey, this film blends romance with humor as two people enter a relationship with secret ulterior motives, only to fall in love for real.
If you’re craving movies like How to Lose a Guy in 10 Days, this list brings you some of the best rom-coms that deliver charm, comedy, and heartfelt romance. From films featuring fake relationships to witty sparring matches between irresistible leads, these movies will keep you entertained and swooning. Plus, if you enjoy more unconventional love stories, check out 10 Best Movies Like Eternal Sunshine of the Spotless Mind, which explore love with a deeper emotional twist.
1. 10 Things I Hate About You (1999)
A modern adaptation of Shakespeare’s The Taming of the Shrew, this teen rom-com follows bad-boy Patrick (Heath Ledger) as he’s paid to date the sharp-tongued Kat (Julia Stiles).
Like How to Lose a Guy in 10 Days, the film thrives on a relationship built on deception that slowly turns into something real. It’s packed with clever humor, great performances, and one of the most iconic romantic gestures in movie history—Ledger’s singing performance of Can’t Take My Eyes Off You.
2. The Proposal (2009)
Sandra Bullock and Ryan Reynolds light up the screen in this hilarious fake-dating rom-com. When a demanding boss (Bullock) forces her assistant (Reynolds) to marry her to avoid deportation, sparks fly in unexpected ways.
Like How to Lose a Guy in 10 Days, The Proposal thrives on comedic tension, an irresistible couple, and unexpected romance.
3. 27 Dresses (2008)
Katherine Heigl plays Jane, a perpetual bridesmaid who suddenly finds herself torn between her long-time crush and a charming reporter (James Marsden).
If you loved Andie’s journalistic ambitions in How to Lose a Guy in 10 Days, you’ll enjoy the career-versus-love conflict in 27 Dresses.
4. Crazy, Stupid, Love. (2011)
This rom-com follows multiple intertwined love stories, with a standout performance from Ryan Gosling as a smooth-talking player who unexpectedly falls for a quirky, independent woman (Emma Stone).
Like How to Lose a Guy in 10 Days, this film delivers romance, humor, and swoon-worthy chemistry.
5. She’s All That (1999)
A high school version of Pygmalion, this classic rom-com follows a popular jock who bets he can turn an “unattractive” girl into prom queen—only to fall for her in the process.
Like How to Lose a Guy in 10 Days, this movie features a relationship that starts as a game but becomes something more.
6. Legally Blonde (2001)
Elle Woods (Reese Witherspoon) transforms herself from a bubbly fashionista into a Harvard Law student to win back her ex—only to discover her own worth along the way.
If you love female-led rom-coms like How to Lose a Guy in 10 Days, Legally Blonde is a must-watch.
7. Failure to Launch (2006)
Another Matthew McConaughey rom-com, this one follows a woman (Sarah Jessica Parker) who is hired to help a man-child move out of his parents’ house but ends up falling for him.
It shares the same humor and sizzling chemistry that made How to Lose a Guy in 10 Days a fan favorite.
8. My Best Friend’s Wedding (1997)
Julia Roberts plays a woman who realizes she’s in love with her best friend—just as he’s about to get married to someone else.
Like How to Lose a Guy in 10 Days, this movie thrives on witty dialogue, mistaken intentions, and a fantastic leading lady.
9. Notting Hill (1999)
Hugh Grant and Julia Roberts star in this heartwarming romance about an ordinary bookstore owner who falls for a famous actress.
Like How to Lose a Guy in 10 Days, this movie is full of charming moments, laugh-out-loud humor, and unforgettable romance.
10. The Ugly Truth (2009)
Katherine Heigl and Gerard Butler engage in a battle of the sexes in this romantic comedy about a cynical TV producer and a cocky relationship expert.
If you loved the playful rivalry in How to Lose a Guy in 10 Days, you’ll enjoy the witty banter and chemistry in The Ugly Truth.
11. Bridget Jones’s Diary (2001)
This beloved rom-com follows Bridget (Renée Zellweger) as she navigates her love life with two very different men (Colin Firth and Hugh Grant).
Like How to Lose a Guy in 10 Days, it features a strong, independent heroine caught in a hilarious love triangle.
12. Friends with Benefits (2011)
Mila Kunis and Justin Timberlake play two friends who attempt a no-strings-attached relationship—only to realize they’ve caught feelings.
Like How to Lose a Guy in 10 Days, this rom-com explores the fine line between playful dating and real love.
13. Clueless (1995)
A modern take on Emma, this film follows Cher (Alicia Silverstone), a stylish and wealthy teen who plays matchmaker but finds herself unexpectedly falling for someone.
Like How to Lose a Guy in 10 Days, Clueless is filled with humor, charm, and a lovable leading lady.
14. Two Weeks Notice (2002)
Sandra Bullock and Hugh Grant shine in this rom-com about a lawyer who’s tired of babysitting her charming but irresponsible boss.
Like How to Lose a Guy in 10 Days, this film is packed with workplace romance, witty banter, and undeniable chemistry.
15. Life as We Know It (2010)
Katherine Heigl and Josh Duhamel play two opposites who must raise a baby together after their best friends pass away.
Like How to Lose a Guy in 10 Days, this film balances humor with heartfelt romance.
If you loved movies like How to Lose a Guy in 10 Days, these rom-coms are sure to bring you joy with their mix of humor, romance, and unforgettable chemistry. Whether you’re drawn to films with fake relationships, strong-willed heroines, or playful romantic rivalries, this list has something for every rom-com fan. And if you’re in the mood for something with a deeper emotional impact, check out 10 Best Movies Like Eternal Sunshine of the Spotless Mind for unconventional love stories that will stay with you long after the credits roll.
